Do the words require italicizing? For what benefit to the customer?
Common typographic convention calls for only the first usage of the word be made to stand out; by being italic or bold. After that, it becomes distracting.
As you mention, there is a need for some semantic value. In this case, it is the first instance of the defined word or phrase. I'd use the <dfn> tag with a title attribute as a redundant definition. For example:
How does the screen reader render <dfn>?
<dt>Art. 10 Address</dt>
<dd><dfn title="the underwriters">We</dfn> are within our legal obligations bij [sic--did you mean "by"?] sending <dfn title="the policy owner">you</dfn> a notification to your last-known address. Thus it is important that you keep us timely informed of your current address, preferably through your <dfn title="the guy who sold you the policy">insurance agent</dfn> so that s/he is also aware of your new address.</dd>